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The Supreme Court on Tuesday explored the tension between Americans' right to free speech and a federal law that prohibits aid to terrorist groups, and hardly anyone seemed clear about the lines of demarcation.

"This is a difficult case for me," allowed Justice Anthony M. Kennedy, whose vote often is the one that decides closely divided cases.

Georgetown law professor David D. Cole, who represents the Humanitarian Law Project, said his clients do not want to provide material support to the groups, but only to help them pursue peaceful ways to end conflict. "The government has spent a decade arguing that our clients cannot advocate for peace, cannot inform about international human rights," Cole told the court.

The project wants to support the lawful activities of the Kurdistan Workers' Party, a militant group in Turkey known as the PKK, and a Sri Lankan group known as the Liberation Tigers of Tamil Eelam. Both are among dozens of organizations on the State Department list, along with better-known groups such as al-Qaeda, Hamas and Hezbollah.

Solicitor General Elena Kagan countered that, as individuals, Cole's clients can advocate whatever they want. But Congress was within its rights, she said, to determine that it was impossible to separate support of any terrorist group's peaceful activities from its violent goals.

"Hezbollah builds bombs. Hezbollah also builds homes," Kagan said. "What Congress decided was when you help Hezbollah build homes, you are also helping Hezbollah build bombs. That's the entire theory behind this statute, and it's a reasonable theory."

Kagan called the law "a vital weapon in this nation's continuing struggle against international terrorism." The government has brought about 150 prosecutions under the law -- half of them successfully.

But the Humanitarian Law Project and its president, Ralph Fertig, a professor at the University of Southern California and a longtime civil rights activist, said it prohibits him and others from giving lawful advice to the PKK about pursuing peaceful means to ending conflict, such as taking disputes to the United Nations.

The case has raised comparisons to McCarthy-era hearings about Americans' association with the Communist Party. The present-day implications of the law, said former president Jimmy Carter, could hurt the Carter Center's efforts to resolve ongoing foreign conflicts.

"Our work to end violence sometimes requires interacting directly with groups that have engaged in it," Carter said in a statement. "Unfortunately, efforts like ours, and those of the many other human rights groups . . . are hindered by the extremely vague 'material support' law that leaves us guessing whether our work to encourage peace could actually be considered illegal."

The U.S. Court of Appeals for the 9th Circuit, based in San Francisco, agreed with Fertig that parts of the law are unconstitutionally vague, singling out those that make it a crime, punishable by up to 15 years in prison, to provide "training," "services" and "expert advice or assistance." Both Fertig's group and the government have asked the Supreme Court to review the decision.